Acid-Catalyzed Diels-Alder Reactions of Cycloalkenones |
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Authors: | Francesco Fringuelli Ferdinando Pizzo Aldo Taticchi Ernest Wenkert |
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Affiliation: | 1. Dipartimento di Chimica , Università di Perugia Via Elce di Sotto , 10, 06100, Perugia, Italy;2. Department of Chemistry , Rice University Houston , Texas, 77001, U.S.A. |
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Abstract: | Whereas the Diels-Alder reaction has been in vogue as a facile method of six-membered ring construction for many years, its application to a one-step cis-octalone synthesis was precluded by discouraging, early reports on the conditions required for the interaction of dienes with 2-cyclohexenones and on the yields of the resultant adducts.1,2 It is quite conceivable that these observations were responsible in part for the minimization of use of an otherwise attractive route toward angularly alkylated six-membered polycycles in the field of steroid total synthesis. The discovery of Lewis acid catalysis of the cycloaddition of α, β-unsaturated carbonyl compounds3 has rekindled interest in the above reactions.4 The following discussion illustrates octalone |
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